Transformative Leadership Conversations with Winnie da Silva

Winnie da Silva
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Transformative Leadership Conversations with Winnie da Silva

Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

  1. "Innovation" with Mauhan Zonoozy

    DEC 18

    "Innovation" with Mauhan Zonoozy

    "Diversity of thought is very powerful. I aggressively seek out people that don’t think like me and are polar opposites of me. That’s the only way to pull yourself out of your own corner." - Mauhan ZonoozyWhat if the biggest barrier to innovation isn’t a lack of ideas—but a fear of permission? In this episode of Transformative Leadership Conversations, I sat down with Mauhan Zonoozy, a strategic advisor and expert in innovation and venture building. Mauhan shared bold perspectives on why permission is a sneaky barrier to innovation—and how leaders can break free from it. We explored why people often wait for a "green light" before acting, how fear of failure holds companies back, and why the best ideas don’t come from rigid playbooks but from fresh thinking and risk-taking. Mauhan also gave us a behind-the-scenes look at how revolutionary leaders think differently, take big bets, and build the kind of confidence that fuels game-changing moves.Hear Mauhan and I discuss:* Stop Asking for Permission: Many people feel the need to ask for permission before taking action—but innovation thrives when people are empowered to move forward without it. This shift in mindset can be transformative for individuals and teams.* The Illusion of Wanting Change: Companies often say they want innovation but get cold feet when change feels risky. Leaders need to recognize this pattern and push through it to create real impact.* Fear is the Real Enemy: Playing it safe is the quickest way to stall innovation. Leaders and teams must be comfortable with the unknown and be willing to face failure head-on. Mauhan reminds us, "If you play scared, that's how you get hurt."* Innovation Isn't a Playbook: While processes and frameworks have their place, real innovation happens when people are given space to think freely. A blank piece of paper and sticky notes may be all you need to spark groundbreaking ideas.* Diversity of Thought is a Superpower: To break out of narrow thinking, you need to bring in diverse perspectives and people who challenge your assumptions. True creativity comes from constructive friction, not echo chambers.* The Courage to Take Big Bets: Revolutionary executives don’t just play it safe—they take risks, often against conventional wisdom. Mauhan points to Amazon’s famous decision to invest in AWS as an example of bold, visionary thinking that changed the industry.* The Hard Truth About Failure: It’s easy to talk about "embracing failure," but living it is much harder—especially when investors or reputations are on the line. True innovators push past the discomfort and stay committed to the process.

    45 min
  2. Creative Friction Sparks Innovation with Sandy Fershee

    DEC 11

    Creative Friction Sparks Innovation with Sandy Fershee

    What if innovation isn’t just for a select few, but something every single person can access and contribute to? In this episode of Transformative Leadership Conversations, I had the chance to chat with Sandy Fershee, the Head of Design & User Experience at Audible. Sandy shared some truly inspiring thoughts about innovation—how it’s not something reserved for just a select few, but something that everyone can contribute to. We talked about the importance of curiosity, creating psychological safety within teams, and how failure is just a part of the process of growth and learning. Sandy also gave some great insights on how diverse perspectives and strong leadership can help unlock creativity and fuel innovation.Listen in as Sandy and Winnie discuss:* Innovation is for Everyone: Innovation doesn’t need to be limited to a special group of people. Everyone, regardless of their role, can offer valuable ideas and contribute to moving things forward.* Creating Psychological Safety: It’s vital to create an environment where people feel safe to experiment, fail, and learn without the fear of judgment.* Curiosity Drives Innovation: Asking questions and digging deeper—always asking "why"—is how you uncover new possibilities and inspire fresh ideas.* Failure as a Learning Opportunity: Failure isn’t the end—it’s part of the journey. By reflecting on what went wrong, we can adjust, learn, and do better next time.* The Power of Diverse Teams: Bringing together people from different backgrounds and disciplines leads to more creative solutions and richer ideas.* Leadership for Innovation: As a leader, it’s crucial to encourage small experiments, fast iterations, and building confidence in ideas. These actions can help keep innovation alive and moving forward.* Sandy’s Passion for Problem-Solving: Sandy’s drive to solve human problems through design and innovation is infectious. She’s all about creating meaningful experiences that make an impact.ResourcesSandy Fershee on LinkedIn (https://www.linkedin.com/in/sandyfershee/) | Audible (https://www.audible.com/about)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/)

    47 min
  3. Discover Your Innovation Style: Take the Quiz!

    DEC 4

    Discover Your Innovation Style: Take the Quiz!

    What if the biggest barrier to innovation within your team or organization is you? In this episode, I’m diving into the heart of innovation—what it means for leaders and how we can create an environment that allows it to thrive. I explore the essential role that leaders play in driving meaningful innovation and reflect on how we can overcome the distractions and barriers that keep us from unlocking our full creative potential.In this episode, you’ll hear about:* The Innovation Leadership Styles Quiz: I introduce a fun and insightful quiz that will help you identify your innovation style, whether you’re a big-picture visionary, a process-driven optimizer, a risk-taking experimenter, a collaborative connector, or a creative playmaker.* The Role of Leadership in Innovation: Innovation is about more than just having good ideas. It's about creating the time, space, and attention necessary for those ideas to come to life. As leaders, we must carve out that space and avoid distractions.* The Importance of Reflection: Understanding your own leadership style is key to unlocking your innovative potential. After you take the quiz, I encourage you to reflect on your strengths and opportunities for growth. Every style has its benefits, but we can all expand our thinking and broaden our approach.* Creating a Culture of Innovation: It’s easy to get caught up in the day-to-day tasks and pressures, but to truly innovate, we need to step back, make space, and give ourselves permission to think creatively. I challenge you to ask yourself: How much innovation are you missing simply because you’re too distracted or busy?Innovation Leadership Style quiz1. When faced with a new challenge, your first instinct is to:A. Imagine an entirely new idea or solution that could disrupt the status quo.B. Look for small, measurable improvements to current products, processes, or ideas.C. Try different approaches to see what works best.D. Assemble a team with diverse perspectives to brainstorm ideas and solutions.E. Infuse energy and excitement into your team to spark creative ideas.2. What’s your preferred approach to brainstorming?A. Share a bold idea and challenge the team to build on it.B. Focus the discussion on solving a specific problem step-by-step.C. Encourage wild ideas, knowing that even "bad" ones might inspire success.D. Facilitate group discussions around new ideas where everyone feels heard.

    13 min
  4. Leadership Branding Wisdom with Maria Ho-Burge

    NOV 27

    Leadership Branding Wisdom with Maria Ho-Burge

    What’s your story, and how does it shape your brand? In this episode of Transformative Leadership Conversations

    41 min
  5. Building Brands with Substance with Andreea Gleeson

    NOV 20

    Building Brands with Substance with Andreea Gleeson

    What does it take to drive change in a male-dominated industry while staying true to your vision? In this episode of Transformative Leadership Conversations, I sit down with Andreea Gleeson, CEO of TuneCore, to hear her remarkable story. Andreea shares how she transitioned from retail to music, the challenges she’s faced as a woman in leadership, and her mission to empower artists at every level of their careers. From tackling gender inequality in the music industry to fostering innovation at TuneCore, Andreea’s journey is one of determination, grit, and vision. Her insights aren’t just inspiring—they’re actionable for anyone looking to lead with purpose and drive change.Listen in as they discuss:* Breaking barriers: Andreea’s work to bring gender parity and representation to the music industry.* Supporting artists: How TuneCore helps musicians, from beginners to global stars, build their careers.* Lessons in leadership: The mindset and skills Andreea honed to grow into her role as CEO.* Empowering growth: The importance of doubling down on your strengths while addressing challenges.* Overcoming obstacles: How Andreea navigated challenges in both her career and in the industry to create lasting change.* The power of confidence: Why confidence is a critical factor for success, especially for women working in competitive spaces.* The art of adaptation: Andreea’s advice on how to stay adaptable and innovative in a constantly changing industry.ResourcesAndreea Gleeson on LinkedIn (https://www.linkedin.com/in/andreeagleeson/) | TuneCore (https://www.tunecore.com/)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | on the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/)

    1h 2m
  6. The Power of Experimentation in Decision-Making with Cherie Hu

    OCT 30

    The Power of Experimentation in Decision-Making with Cherie Hu

    How do I define success—and how does that shape the decisions I make? In this episode of Transformative Leadership Conversations, I have the pleasure of chatting with Cherie Hu, a music industry expert and the founder of Water & Music. Together, we dive into decision-making in both creative and business landscapes, exploring how our interpretations of success can shape our paths and the strategies we choose.You’ll here them discuss:* Redefining Success: Leaders should understand that success can be defined in various ways depending on context, extending beyond just revenue metrics to include broader impacts and outcomes.* Balancing Risk and Stability: Having a stable foundation is crucial for organizations, as it allows leaders to take calculated creative risks without putting their well-being or financial health at risk.* Value of Experimentation: Embracing iterative experiments provides valuable insights and data, helping leaders make informed decisions and refine their strategies more effectively.* The Power of Storytelling: Leaders can effectively communicate difficult decisions and rally support by crafting compelling narratives that make complex truths more relatable and understandable.* Influence of Culture and Values: The culture of a company and its commitment to social impact significantly shape decision-making processes and how relationships with stakeholders are developed and maintainedResources:Cherie Hu on the (https://www.waterandmusic.com/)Web (https://www.waterandmusic.com/) I (https://x.com/cheriehu42)X (Twitter) (https://x.com/cheriehu42) I (https://www.linkedin.com/in/cheriehu/)LinkedIn (https://www.linkedin.com/in/cheriehu/)Winnie da Silva on (https://www.linkedin.com/in/winnie-da-silva-1b8414/)LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) I (https://www.winniedasilva.com/)Web (https://www.winniedasilva.com/)

    47 min
  7. Indecisiveness is Cancer: Decision-Making Insights with Prita Kumar

    OCT 23

    Indecisiveness is Cancer: Decision-Making Insights with Prita Kumar

    What happens when the very decisions you make as a leader cause unintended ripple effects throughout your organization? In this episode of Transformative Leadership Conversations, I sit down with Prita Kumar to explore the complex balance of short-term goals, long-term planning, and the law of unintended consequences in leadership. Prita shares her experience in managing teams without overwhelming them, how she thinks about qualitative vs. quantitative data, and why creating consistency across departments is crucial for success.You will hear them talk about:* Prioritizing Team Focus: Leaders must be mindful of how much they ask from their teams to avoid overwhelming them with conflicting priorities.* Balancing Short-Term vs. Long-Term Goals: In resource-rich environments, leaders can plan for the long term, but in leaner times, focusing on immediate goals becomes critical.* Qualitative vs. Quantitative Metrics: Success metrics are key to decision-making, and even qualitative decisions should be supported by some form of data.* Leadership Messaging: Leaders need to ensure that directives across departments don’t conflict, as this can cause operational inefficiencies.* Learning from Experience: Prita advises young leaders to build diverse support systems to balance different perspectives before making key decisions.Resources:Prita Kumar on (https://www.linkedin.com/in/pritakumar/)LinkedIn (https://www.linkedin.com/in/pritakumar/)Winnie da Silva on (https://www.linkedin.com/in/winnie-da-silva-1b8414/)LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) I Website (https://www.winniedasilva.com/)

    44 min
  8. Mastering Leadership Decision-Making

    OCT 16

    Mastering Leadership Decision-Making

    What if the decisions you make as a leader are only addressing half the problem? In this episode of Transformative Leadership Conversations, I explore the hidden complexities beneath the surface of leadership challenges and how understanding those deeper issues can lead to more effective decision-making. I talk about the importance of not just focusing on what’s immediately visible but also considering the less obvious factors that might be driving the situation. By adopting a more thoughtful, strategic approach, leaders can avoid impulsive reactions and create more sustainable solutions.Key Points:* The Iceberg Analogy: Most of a problem’s complexity is hidden below the surface, just like an iceberg. As a leader, you need to be curious and dig deeper to uncover the real issues before jumping to conclusions.* Decision Fatigue: Decision-making can be exhausting, especially after a full day of thinking and problem-solving. I discuss how prioritizing decisions and building routines can help you stay sharp and avoid burnout.* Cognitive Switching: While switching between tasks can sometimes inspire creativity, too much of it can drain your mental energy. I share tips on grouping similar tasks and minimizing digital distractions to stay more focused and productive.* The Power of Routine: Establishing a consistent decision-making routine can streamline your thought process and free up mental energy for bigger issues.* Anticipating Hidden Challenges: Leaders must look beyond the surface of any problem, anticipating and addressing the unseen obstacles that can affect the outcome.* Effective Decision-Making: Clear and structured decision-making processes aren’t just for you—they help keep your team on the same page and reduce confusion. I talk about how to communicate decisions effectively and ensure alignment across your organization.ResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/)Books mentioned:- The Decision Book: Fifty Models for Strategic Thinking by Mikael Krogerus and Roman Tschäppeler- Thinking, Fast and Slow by Daniel Kahneman

    30 min
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Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

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